Electrolytic preparation of 3-amino-2-oxazolidones



United States Patent ELECTROLYTIC PREPARATION OXAZOLIDONES Gabriel Gever, Oxford, N. Y., assignor, by mesne assignments, to The Norwich Pharmacal Company, Norwich, N. Y a corporation of New York No Drawing. Original application February 28, 1952, Serial No. 274,067, now Patent No. 2,652,402, dated September 15, 1953. Divided and this application July 29, 1953, Serial No. 371,173

1 Claim. (Cl. 204-74) OF 3-AMINO-2- wherein R is a member of the alkyl and hydroxy (lower) alkyl R, is a member of the group consisting of hydrogen,

lower alkyl and hydroxy (lower) alkyl R is a member of the group consisting of hydrogen,

lower alkyl and hydroxy (lower) alkyl, and

R is a member of the group consisting. of hydrogen,

lower alkyl and hydroxy (lower) alkyl The new compounds of the series are particularly useful as intermediates for the preparation of members of a series of N-(5-nitro-2-furyl)alkylidene-3-amino-2- oxazolidones, notably, N-(5-nitro-2-furfurylidene)-3- amino-2-oxazo1idone, which I have invented and which form the subject of my co-pending application, Serial No. 274,066, filed February 28, 1952, now Patent No. 2,742,462. This application is a division of my co-pending application Serial No. 274,067, filed February 28, 1952, now Patent No. 2,652,402.

The various members of the new series of 3-amino- 2-oxazolidones can be prepared by the electrolytic reduction of the corresponding 3-nitro-2-oxazo1idone derivative. In this method, sulfuric acid is employed as the catholyte, lead as the anode, a mercury pool as the cathode, and a current density of 0.204 amp./cm. is used for one hour at a temperature of 5 to C. This reduction produces the desired 3-amino-2-oxazolidone derivative from the corresponding 3-nitro-2-oxazolidone.

In order that my invention may to those skilled in the art, the preparation of members of the new series compound 3-amino-4,4-dimethyl-2-oxazolidone, by the method which I have invented is described briefly:

EXAMPLE I 3-amino-2-oxazolidone HzN-N'- C: O

0 Tar-C group consisting of hydrogen, lower 2,852,451 Patented Sept. 16, 1958 ice.

3-nitro-2-oxazolidone is reduced electrolytically, using cc. of 10% sulfuric acid as the catholyte, a lead anode, a mercury pool cathode and a current density of 0.204 amp./cm. for one hour at a temperature of 5 10 C. At the end of this time the aqueous solution is separated from the mercury.

EXAMPLE II 3-amino-4,4-dimethyl-2-oxazolidone H2NNCO Cs CH3 a 3-amino-2-oxazolidone which comprises electrolytically reducing a 3-nitro-2- oxazolidone represented by the formula:

have the significance above 3-nitro-2-oxazo1idone in a wherein R, R R and R given, by suspending the catholyte of dilute sulfuric acid connected with a lead anode and a mercury pool cathode, and using a current of a density of about 0.204 amp/cm. at a temperature of about 5-10 C.

References Cited in the file of this patent UNITED STATES PATENTS 

